My fiance (then wife) will be traveling to Japan for 10 nights in early May 2016 (we're landing May 5, the last day of Golden Week which is unavoidable since we will be first visiting family in Hong Kong and this is the only time that works for them). Due to flight schedules, we're going to flying into Osaka and back home from Tokyo (BA points on Cathay to KIX, AA points on JAL (hopefully first) to JFK).

My plan is to spend 5 nights in either Kyoto or Osaka, and the last 5 nights in Tokyo staying at all Starwood hotel, and do day trips from both destinations. I've heard varying things about both Kyoto and Osaka, in that Kyoto has more to do and see, but is dead at night, while Osaka is the opposite. While we're in our early 30s, and we appreciate beautiful sights, we want to at least have the option of doing something at night (but if Osaka is good for nothing else, we can skip it or do a day trip there). Also, we love food, so that will play into our decision making as well.

In your opinion, is there a clear-cut winner between Osaka and Kyoto? Do you think the trip is relatively well planned, and, if it were you, where would you spend your first 5 nights in Japan?

Thanks!